Great Lakes Luxury Vacations
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Top Luxury vacation packages in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥243,866, price is now ￥213,174 per person
￥213,174
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The staff is incredible. We always enjoy staying here!
Reviewed on Feb 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥310,404, price is now ￥260,047 per person
￥260,047
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥315,934, price is now ￥266,546 per person
￥266,546
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
The Pfister Hotel
Downtown Milwaukee
Price was ￥455,107, price is now ￥396,882 per person
￥396,882
per person
Mar 24 - Mar 30
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Milwaukee (MKE)
9.6/10 Exceptional! (1,786 reviews)
Great welcome by Kristin kicked it off! So accommodating and warm. The room which I upgraded to a suite was perfect on the top floor. Food was tasty and the location made it easy to walk to Fiserv and other restaurants!
Reviewed on Feb 8, 2026
Potawatomi Hotel & Casino
Menomonee River Valley
Price was ￥386,243, price is now ￥342,604 per person
￥342,604
per person
Mar 24 - Mar 30
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Milwaukee (MKE)
9/10 Wonderful! (1,357 reviews)
Room was clean and beautiful!! Front desk staff was helpful and has one of the best selections of slot machines in the casino will definitely be going back!!!
Reviewed on Feb 7, 2026
5* Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥310,404, price is now ￥260,047 per person
￥260,047
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥315,934, price is now ￥266,546 per person
￥266,546
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
1 Hotel Toronto
Downtown Toronto
Save 100% on your flight
Price was ￥511,178, price is now ￥274,088 per person
￥274,088
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Toronto (YYZ)
9.4/10 Exceptional! (632 reviews)
1Hotel is my favourite hotel in Toronto. Always immacualte and customer service is top notch
Reviewed on Feb 6, 2026
3 Night Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥243,866, price is now ￥213,174 per person
￥213,174
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The staff is incredible. We always enjoy staying here!
Reviewed on Feb 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥310,404, price is now ￥260,047 per person
￥260,047
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥315,934, price is now ￥266,546 per person
￥266,546
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
4 Night Luxury vacations in Great Lakes
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥451,858, price is now ￥346,480 per person
￥346,480
per person
May 1 - May 5
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥431,726, price is now ￥339,944 per person
￥339,944
per person
May 1 - May 5
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Top Luxury Great Lakes Hotels
The Omni King Edward Hotel
37 King St E Toronto ON
Discover luxurious lodging at The Omni King Edward Hotel, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. Deluxe amenities ...
9.6/10 Exceptional! (2,467 reviews)
a favorite place to stay as it is elegant and they take care of you.
Reviewed on Feb 4, 2026
Fairmont Royal York
100 Front St West Toronto ON
Treat yourself to a luxury stay at Fairmont Royal York, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 3 bars, indoor ...
9/10 Wonderful! (7,724 reviews)
great staff, beautiful property
Reviewed on Feb 3, 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Trump International Hotel & Tower Chicago is a lush 5-star boutique property where you can be treated to deep soaking bathtubs and pillowtop beds. The spa, indoor ...
9.4/10 Exceptional! (1,841 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
